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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:56:21 UTC
Update Date2019-07-23 06:19:48 UTC
HMDB IDHMDB0035893
Secondary Accession Numbers
  • HMDB35893
Metabolite Identification
Common NameElaterinide
DescriptionElaterinide, also known as colocynthin or coloside a, belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. Elaterinide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862788
Synonyms
ValueSource
alpha-Elaterin 2-D-glucopyranosideHMDB
beta-Glucoside de la curcurbitaine (e)HMDB
ColocynthinHMDB
Coloside aHMDB
Cucurbitacin e 2-O-beta-D-glucopyranosideHMDB
Cucurbitacin e-2-O-glucosideHMDB
CUEGHMDB
Elaterin, 2-beta-glucopyranosideHMDB
GratiotoxinHMDB
2-O-beta-D-Glycopyranosyl-cucurbitacin eHMDB
(3E)-6-Hydroxy-6-(13-hydroxy-1,6,6,11,15-pentamethyl-5,17-dioxo-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,7-dien-14-yl)-2-methyl-5-oxohept-3-en-2-yl acetic acidGenerator
ElaterinideMeSH
Chemical FormulaC38H54O13
Average Molecular Weight718.8276
Monoisotopic Molecular Weight718.356441814
IUPAC Name(3E)-6-hydroxy-6-(13-hydroxy-1,6,6,11,15-pentamethyl-5,17-dioxo-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,7-dien-14-yl)-2-methyl-5-oxohept-3-en-2-yl acetate
Traditional Name(3E)-6-hydroxy-6-(13-hydroxy-1,6,6,11,15-pentamethyl-5,17-dioxo-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,7-dien-14-yl)-2-methyl-5-oxohept-3-en-2-yl acetate
CAS Registry Number1398-78-3
SMILES
CC(=O)OC(C)(C)\C=C\C(=O)C(C)(O)C1C(O)CC2(C)C3CC=C4C(C=C(OC5OC(CO)C(O)C(O)C5O)C(=O)C4(C)C)C3(C)C(=O)CC12C
InChI Identifier
InChI=1S/C38H54O13/c1-18(40)51-33(2,3)13-12-25(42)38(9,48)30-21(41)15-35(6)24-11-10-19-20(37(24,8)26(43)16-36(30,35)7)14-22(31(47)34(19,4)5)49-32-29(46)28(45)27(44)23(17-39)50-32/h10,12-14,20-21,23-24,27-30,32,39,41,44-46,48H,11,15-17H2,1-9H3/b13-12+
InChI KeyQKEJRKXVLGOJMB-OUKQBFOZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentCucurbitacin glycosides
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point148 - 150 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.046 g/LALOGPS
logP2.28ALOGPS
logP1.18ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)12.13ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area217.35 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity185.03 m³·mol⁻¹ChemAxon
Polarizability76.54 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zg0-0101094600-9d6563108d0ea06e8d42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4s-0403793100-3d51a4216af82b8bce4aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-2609781000-25c06c7b5faea5bacc0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0aos-4900044300-c61b10c983514ff11bc5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-5900051000-1b76b9ba2125c4a3a80cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9202260000-ccaade6a2fb9d18e16c9Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014678
KNApSAcK IDC00030029
Chemspider ID4740095
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5901827
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.